Carbanions, generally involved as ion pairs, are important intermediates in the organic synthesis of many biologically active natural products, pharmaceuticals, drugs, etc. A common procedure is the metallation of a substrate with an alkyl lithium or lithium amide in an ether followed by reaction with a suitable electrophile. We propose to put this largely empirical technique on a quantitative basis with answers to the question: How do equilibrium ion pair carbon acidities vary as a function of structure, solvent temperature and gegenion? We propose to determine equilibrium constants for the reactions, R M + R'H = R'-M+ + RH, for a group of indicator hydrocarbons (e.g. fluorene, arylmethanes) in tetrahydrofuran (THF) with cesium as the gegenion; Cs+ is known to form contact ion pairs that are readily interpreted. The approach will be extended to other functional groups important in synthesis: vinyl, allyl, benzyl and aryl systems, sulfur, silicon and phosphorus compounds, amides, ethers and dianion systems. The studies will be extended to the corresponding lithium compounds. Li+ is involved in varying kinds of ion pairs but structural understanding will be facilitated by comparison with the more straight-forward Cs+ ion pairs. The above Carbanion studies will then be extended to enolate ions. Conductivity studies will relate the ion pairs to the dissociated ions. The results will be interpreted with the help of related kinetic acidity measurements and theoretical quantum chemical calculations.